(−)‐Daucic Acid: Revision of Configuration, Synthesis, and Biosynthetic Implications | Zendy

Lichtenthaler Frieder W. | Zendy; Nakamura Katsumi | Zendy; Klotz Jürgen | Zendy

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(−)‐Daucic Acid: Revision of Configuration, Synthesis, and Biosynthetic Implications

Author(s) -

Lichtenthaler Frieder W.,

Nakamura Katsumi,

Klotz Jürgen

Publication year - 2003

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200352718

Subject(s) - stereochemistry , galactose , carbon atom , mannose , chemistry , biosynthesis , biochemistry , organic chemistry , gene , ring (chemistry)

The synthesis of dihydropyrans with the D ‐ xylo ( 1 ), D ‐ ribo , L ‐ arabino , and D ‐ lyxo ( 2 ) configuration by one‐carbon‐atom homologation of D ‐mannose or D ‐galactose, terminal oxidation, and directed β elimination revealed (−)‐daucic acid isolated from carrots to be 2 , rather than 1 as previously thought. The identical configuration of 2 and KDO 8‐P ( 3 ) and available biosynthetic information about chelidonic acid ( 4 ) suggest a KDO 8‐P based pathway for the generation of 2 and 4 in plants.

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